Abstract
Several 4-arylidene-2-phenyl-5(4H)-azlactones have been synthesized via Erlenmeyer method. The synthesized compounds have been characterized on the basis of systematic spectral studies (IR, H-1 NMR, C-13 NMR, and MS). The compound (4Z)-4-(3,5-dimethoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one, C18H15NO4, (5), crystallizes in the orthorhombic system, space group P2(1)2(1)2(1), with a = 5.6793(3) angstrom, = 15.2038(7) angstrom, c = 17.6919(10) angstrom, Mr = 309.31, V = 1527.64(14) angstrom(3), Z = 4 and R = 0.0547. The compound (4Z)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one, C19H17NO5, (6) crystallizes in triclinic geometry with space group P-1, having unit cell parameters a = 7.3814(3) angstrom, b = 8.1446(3) angstrom, c = 13.9845(5) angstrom, alpha = 86.918(3), beta = 83.314(2), gamma = 82.462(3), Mr = 339.34, V = 827.16(5) angstrom(3), Z = 2 and R = 0.0433. The DFT calculations of compounds (5) and (6) have been carried out to ascertain the stability of Z-conformer. The in vitro antimicrobial activity of all the compounds (1-6) was evaluated by the disk diffusion method against gram +ve and gram -ve microorganism and fungal strains. The MIC of the synthesized compounds was determined by agar well diffusion method in 96-well microtiter plate. All the synthesized compounds were also screened for their free radical scavenging activity by DPPH method. (C) 2012 Elsevier B.V. All rights reserved.